109786-73-4Relevant articles and documents
Synthesis of Fluorine-Containing Analogues of 1-Lysoglycerophospholipids via Horner-Wadsworth-Emmons Reaction
Nakao, Michiyasu,Tanaka, Kazue,Kitaike, Syuji,Sano, Shigeki
, p. 3654 - 3661 (2017)
An efficient method of synthesizing fluorine-containing analogues of 1-lysoglycerophospholipids (1-LPLs) by introducing a palmitoyl moiety starting from bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent) is described. The method effectively
Syntheses of polymerizable monoacylglycerols and 1,2-diacyl-sn-glycerols
Srisiri, Warunee,Lamparski, Henry G.,O'Brien, David F.
, p. 5911 - 5915 (1996)
The first chemical syntheses of polymerizable monoacylglycerol and 1,2-diacyl-sn-glycerol are reported. The monodienoylglycerol is obtained in 80% yield from 1,2-O-isopropylidene-sn-glycerol and dienoyl fatty acid. The dienoic acid is accessible in 60% yield from the base-catalyzed hydrolysis of dienoyl ester, which is synthesized from the Wittig-Horner reaction of aldehyde and trimethyl 4-phosphonocrotonate. The acylation is carried out in the presence of 4-(dimethylamino)pyridine and dicyclohexylcarbodiimide. The use of excess protected glycerol relative to fatty acid affords the acylated product in high yield. The final step is the deprotection of isopropylidene group using dilute HCl solution. The 1,2-diacyl-sn-glycerol is synthesized by acylation of 3-(4-methoxybenzyl)-sn-glycerol with dienoyl fatty acid in the presence of 4-(dimethylamino)pyridine and dicyclohexylcarbodiimide. The removal of the 4-methoxybenzyl group by dimethylboron bromide catalyzed hydrolysis is especially useful in the synthesis of polymerizable lipids because the deprotection proceeds without any apparent effect on the dienoyl polymerizable group and without detectable isomerization of 1,2-diacylglycerol to 1,3-diacylglycerol. The overall yield for the synthesis of the polymerizable 1,2-diacyl-sn-glycerol from the dienoyl fatty acid is ca. 50%.
The Chiral Target of Daptomycin Is the 2R,2′S Stereoisomer of Phosphatidylglycerol
Moreira, Ryan,Taylor, Scott D.
, (2021/12/09)
Daptomycin (dap) is an important antibiotic that interacts with the bacterial membrane lipid phosphatidylglycerol (PG) in a calcium-dependent manner. The enantiomer of dap (ent-dap) was synthesized and was found to be 85-fold less active than dap against
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
supporting information, p. 12939 - 12945 (2019/08/22)
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
